Clif Mathews

Questioner
DISC Type : c

Partner | Mergers & Acquisitions | Keynote Speaker & Executive Coach at Deloitte

Greater Boston, United States

Overview

Clif Mathews is a Partner at Deloitte with 25 years of experience in Mergers & Acquisitions and advisory services. He is also a keynote speaker and executive coach, focusing on guiding senior executives through major transitions. People who have worked with him describe him as dedicated, hard-working, and proactive.

Clif is passionate about leadership development beyond his role at Deloitte, having founded the "Second Summit Brief" to share his insights. He focuses on helping accomplished leaders redefine success and move forward when they feel stuck. A unique learning experience for him was studying abroad during his time at Louisiana College.

He developed the concept of "The Success Trap, " where the very habits that build a leaders career become what holds them back.

Personality Overview

Systematic

Value Seeker

Cautious & Analytical

They prefer to fully evaluate every situation.  It is quite likely of them to ask for pricing or other concessions. While they don't hesitate to ask questions, they are generally risk-averse and tend to be late adopters.

Topics They Care About

The Success Trap
This is his core coaching philosophy, focusing on helping successful leaders overcome career plateaus by changing the habits that once served them.
Leadership Communication
He frequently writes about the importance of clear messaging for leaders to build influence and drive action within their organizations.
M&A Advisory
As a Partner at Deloitte with 25 years of experience, this is his core area of expertise, where he advises executives through major transactions.

Media Appearances

Clif has no verified media appearances

Work History

9-2002
Partner | Mergers & Acquisitions | Keynote Speaker & Executive Coach at Deloitte
6-2025
Founder at Second Summit Brief
9-2025
Thought Leader Member at Archimedes

Education

1998 - 2002
BBA from Louisiana College

More Information

Social Presence :

Prographics :

Exp : 23 Location : Greater Boston, United States Job Level : N/A Designation : Partner | Mergers & Acquisitions | Keynote Speaker & Executive Coach at Deloitte
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Insights For Selling To Clif

During A Call Or A Meeting

DO's

  • Keep some extra margin in hand as they will likely negotiate the pricing
  • Emphasize on objective proof of ROI, help them do a thorough evaluation
  • Emphasise more on facts and measurable benefits

DONT's

  • Avoid rushing them, be polite and patient
  • Don’t depend too much on anecdotal evidence, it reduces their confidence
  • Don’t overhype the product/pitch, keep it measured

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Clif is

  • Ensuring that the product delivers ROI, cost-effective pricing and process compliance are very important for them.
  • Will you ever get a clear answer from Clif

  • It doesn’t come naturally to them but they can say no if they are not convinced.

Insights For Deal Planning

    How fast (or slow) will Clif move?

  • If they have the information that they need, they can move fast at making their decisions.
  • Can Clif take some risk or not?

  • If they believe that they have analyzed the situation well, they can take a little risk.

You And Clif

Personality Compatibility


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